Selective Silylation of Nitriles with an NHC-Stabilized Silylene to 1,2-Disilylimines and Subsequent Synthesis of Silaaziridines

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• 作者：Jianfeng Li ; Bing Ma ; Chunming Cui
• 刊名：Organometallics
• 出版年：2016
• 出版时间：May 23, 2016
• 年：2016
• 卷：35
• 期：10
• 页码：1358-1360
• 全文大小：280K
• 年卷期：0
• ISSN：1520-6041

文摘

The highly regioselective synthesis of trans-1,2-disilylimines have been achieved by the bis-silylation of nitriles with the NHC-stabilized silylene NHC-Si(NArSiMe₃)Cl (1; Ar = 2,6-iPr₂C₆H₃, NHC = 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene). The bis-silylation involves the migration of the SiMe₃ group on the nitrogen atom in the silylene to the carbon atom of the nitrile functionality. The 1,2-disilylimine products feature an NHC-stabilized silaimine moiety and could undergo nucleophilic attack by phenyllithium reagents to yield novel silaaziridines with an NHC-stabilized exocyclic Si═N double bond.